Potassium Hydroxide → 2,4-Dimethyl-5-carboxy-1H-pyrrole-3-propanoic acid 5-ethyl ester

HRID 1860730ノート

反応式

HRID 1860730 の反応式
[CH3:1][C:2]1[NH:3][C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:5]([CH3:14])[C:6]=1[CH2:7][CH2:8][C:9]([O:11]CC)=[O:10].[OH-].[K+]>O.CO>[CH2:18]([O:17][C:15]([C:4]1[NH:3][C:2]([CH3:1])=[C:6]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[C:5]=1[CH3:14])=[O:16])[CH3:19]

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 291761Ethyl 2,4-dimethyl-5-(ethoxycarbonyl)-3-pyrrolepropionate

生成物 1

HCID 1422052,4-Dimethyl-5-carboxy-1H-pyrrole-3-propanoic acid 5-ethyl ester収率 80.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 962Water溶媒2 回

反応条件

温度
70 °C

実験手順

To a suspension of 10 g (38.9 mmol) ethyl 2,4-dimethyl-5-(ethoxycarbonyl)-3-pyrrolepropionate (commercially available) in a mixture of water (250 mL) and methanol (MeOH) (50 mL) was added 3.0 g of KOH in 50 mL of water. The mixture was stirred at 70° C. for 4 hr. The reaction mixture was cooled and the methanol was stripped from the mixture under vacuum. The remaining solution was filtered and the filtrate was then acidified with 6N hydrochloric acid to pH 3. The precipitate which formed was collected by filtration, washed with a 2:1 mixture of water and ethanol and dried under vacuum to give 7.5 g of 4-(2-carboxy-ethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester as a white solid.

後処理

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe remaining solution was filtered
  3. customThe precipitate which formed
  4. filtrationwas collected by filtration
  5. washwashed with a 2:1 mixture of water and ethanol
  6. customdried under vacuum

出典と根拠

ORDレコード
ord-d9f8275b2f9d4075804d561694b916c3
出典データセット
uspto-grants-2003_03
特許番号
US06531502B1

反応ノート

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